Process for the preparation of organic nitriles from organic carboxylic acid primary amides

Abstract

This invention relates to a process for the preparation of organic nitriles. More particularly, the invention relates to a process for the preparation of organic nitriles by reacting organic carboxylic acid primary amides with a dehydrating agent in the presence of a catalytic amount of a particular quaternary ammonium salt.

We claim: 
     
       1. A homogeneous process for preparing organic nitriles which comprises reacting an organic carboxylic acid primary amide selected from the group consisting of aliphatic carboxylic acid primary amide, cycloaliphatic carboxylic acid primary amide, heterocyclic carboxylic acid primary amide and aromatic carboxylic acid primary amide containing about 2 to about 22 carbon atoms with at least a stoichimetric amount of a dehydrating agent at a tenperature of about 25° C. to 90° C. in the presence of a catalytic amount of a quaternary ammonium salt having the formula: ##STR2## wherein R 1 , R 2 , R 3 , and R 4  are each independently selected from alkyl of from 1 to 18 carbon atoms, alkylaryl of from 7 to 18 carbon atoms, arylalkyl of from 7 to 18 carbon atoms, and aryl of from 6 to 18 carbon atoms and X is an anion. 
     
     
       2. A process according to claim 1 wherein said dehydrating agent is thionyl chloride. 
     
     
       3. A process according to claim 2 wherein said quaternary ammonium salt is benzyltriethylammonium chloride. 
     
     
       4. A process according to claim 2 wherein said organic carboxylic acid primary amide is an aromatic carboxylic acid primary amide containing about 7 to about 22 carbon atoms. 
     
     
       5. A process according to claim 4 wherein said aromatic carboxylic acid primary amide is substituted or unsubstituted benzamide. 
     
     
       6. A process according to claim 5 wherein said substituted or unsubstituted benzamide is benzamide. 
     
     
       7. A homogeneous process for preparing organic nitriles which comprises reacting an organic carboxylic acid primary amide selected from the group consisting of aliphatic carboxylic acid primary amide, cycloaliphatic carboxylic acid primary amide, heterocyclic carboxylic acid primary amide and aromatic carboxylic acid primary amide containing about 2 to about 22 carbon atoms with at least a stoichiometric amount of a dehydrating agent at a temperature of about 25° C. to 90° C. in the presence of a quaternary ammonium salt having the formula ##STR3## wherein R 1 , R 2 , and R 3  each independently contain 1 to 4 carbon atoms and R 4  contains 1 to 4 carbon atoms or a benzyl group and X is halide, hydrogen sulfate, perchlorate or hydroxide anion. 
     
     
       8. A process according to claim 7 wherein said dehydrating agent is thionyl chloride. 
     
     
       9. A process according to claim 8 wherein said quaternary ammonium salt is benzyltriethylammonium chloride. 
     
     
       10. A process according to claim 9 wherein said organic carboxylic acid primary amide is an aromatic carboxylic acid primary amide containing about 7 to about 22 carbon atoms. 
     
     
       11. A process according to claim 10 wherein said aromatic carboxylic acid primary amide is substituted or unsubstituted benzamide. 
     
     
       12. A process according to claim 11 wherein said substituted or unsubstituted benzamide is benzamide.